Windham, VT Homes

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  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
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• 

  

  

  /41

  $545,000 Sold Jul 18, 2025

  • 2,450 Sq Ft
  • $222/SF
  • 48 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1880

  441 Guilford St, Brattleboro, VT 05301

  Perched proudly on a knoll, this mid-19th-century colonial was one of two farmsteads in this neighborhood of Brattleboro, VT. This stunning, 4-BR, 2-BA hip roof colonial & spacious, 2-story barn have been lovingly cared for by the same owner for 56 years! Now is your opportunity to own a New England classic in a neighborhood setting, but country feel - all w/in very close proximity to town

  Dan Normandeau Berkley & Veller Greenwood Country

  441 Guilford St, Brattleboro, VT 05301
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  /38

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,410 Sq Ft

  773 Guilford St, Brattleboro, VT 05301

  773 Guilford St, Brattleboro, VT 05301
• 

  

  /2

  $89,000

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
• 

  

  

  /25

  $349,000 Sold Jul 15, 2025

  • 1,503 Sq Ft
  • $232/SF
  • 42 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1928

  6 Willow St, Brattleboro, VT 05301

  This home truly has it all and is conveniently located on one Brattleboro's most charming streets. Close to shopping, restaurants, and downtown yet tucked away from it all. The large fenced lot has good exposure for gardening. Inside the home you will find 3 bedrooms and a fabulous renovated attic, complete with custom cabinetry and shelving. Enjoy indoor/outdoor entertaining with french-door

  John Hatton Berkley & Veller Greenwood Country

  6 Willow St, Brattleboro, VT 05301
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  /32

  Est $404,573 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  348 Green River Rd, Brattleboro, VT 05301

  348 Green River Rd, Brattleboro, VT 05301
• 

  

  /10

  $175,000

  • Land
  • 8 Acres
  • $21,875 per Acre

  680 W River Rd, Brattleboro, VT 05301

  8 acres only 2 miles from Brattleboro situated across the road from the West River. Existing gated gravel driveway is in. Gravel on site and road roughed into a high plateau with designs for SIX 1-2 bedroom cottages. Topographical survey, septic design plans and other existing engineering are complete which make this an attractive option for someone looking to develop a parcel into a cottage

  Chris Long BHG Masiello Brattleboro

  680 W River Rd, Brattleboro, VT 05301
• 

  

  /60

  $130,000 Sold Jul 15, 2025

  • 1,392 Sq Ft
  • $93/SF
  • 204 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  7 Deepwood Park, Brattleboro, VT 05301

  Price improvement!!! Charming one level mobile home with addition in Tri Park Co-op. 3 bedrooms, 2 bathrooms, eat in kitchen, large living room, den/other room, large back deck for entertaining and BBQs and a full concrete foundation!!! Great property! Don't miss this opportunity! Seller to pay buy in fee to the park for buyer at time of closing!!!

  Emily Lagerberg R.H. Thackston & Company

  7 Deepwood Park, Brattleboro, VT 05301
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  /35

  Est $395,988 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,272 Sq Ft

  73 Clark Rd, Brattleboro, VT 05301

  73 Clark Rd, Brattleboro, VT 05301
• 

  

  /18

  $176,500

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  15 Lynwood Dr, Brattleboro, VT 05301

  This is absolutely NOT your ordinary Mobile Home! The original steel frame is the only remaining component of the mobile home. Completely rebuilt from the floor up with wood framing, windows, doors and insulation. This fully fenced leased lot has two sheds, a 1 car garage building with tons of storage and a workshop building with its own mini-split for heat and AC. The tastefully renovated

  Chris Long BHG Masiello Brattleboro

  15 Lynwood Dr, Brattleboro, VT 05301
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  /10

  $40,000 Sold Jul 14, 2025

  • Land
  • 0.29 Acre
  • $137,931 per Acre

  • 2 Days On Market

  42-44 Canal St, Brattleboro, VT 05301

  .31 Acre lot in downtown Brattleboro with 4 rental storage units. Storage units with parking lot can bring in ~10K+ of revenue if used as such, or lot is perfect for townhome development, which is highly supported by the Town. Storage units rents can rent at $150 each. The lot recently appraised at $45,000 (please e-mail for appraisal). Parking lot currently used by residents of adjacent

  Michael Gilman 3GEN Real Estate Inc

  42-44 Canal St, Brattleboro, VT 05301
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  /34

  Est $554,294 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,500 Sq Ft

  1245 Black Mountain Rd, Brattleboro, VT 05301

  1245 Black Mountain Rd, Brattleboro, VT 05301
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  /9

  $80,250

  • Land
  • 3.10 Acres
  • $25,887 per Acre

  0 E Orchard St Unit 5047716, Brattleboro, VT 05301

  A rare opportunity to purchase a lot in a highly desirable Brattleboro neighborhood. This 3+ acre wooded parcel features a mature pine forest with additional hardwoods intermixed, stonewalls and even a small stream. It's the location that makes this property unique. Just up the road from the Brattleboro Country Club on a quiet street that gives quick access to all that Brattleboro and the

  Bill Hickok Berkley & Veller Greenwood Country

  0 E Orchard St Unit 5047716, Brattleboro, VT 05301
• 

  

  /23

  $93,999 Sold Jul 14, 2025

  • 880 Sq Ft
  • $107/SF
  • 118 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  8 Deepwood Park, Brattleboro, VT 05301

  Welcome to 8 Deepwood Dr, Brattleboro, VT 05301, where modern comfort meets affordability in Deepwood MHP Park! This brand-new Dias model manufactured home offers 3 bedrooms, 2 bathrooms, and 869 sq. ft. (14 x 66 ft.) of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  8 Deepwood Park, Brattleboro, VT 05301
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  /22

  Est $295,280 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  1075 Middle Rd, Brattleboro, VT 05301

  1075 Middle Rd, Brattleboro, VT 05301
• 

  

  /60

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,731 Sq Ft

  49 Tyler St, Brattleboro, VT 05301

  Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

  Dan Normandeau Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301
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  /48

  $310,000 Sold Jul 14, 2025

  • 1,300 Sq Ft
  • $238/SF
  • 57 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1924

  52 Belmont Ave, Brattleboro, VT 05301

  Step into this beautifully updated Cape style home offering a perfect blend of classic charm and modern updates. Ideally located near the hospital, public transportation, shopping and more, providing both convenience and comfort in an ideal location. From the moment you enter, you’ll be greeted by the warm inviting ambiance, fall in love with the stunning wood flooring and rich natural woodwork

  Kerry Mulverhill Brattleboro Area Realty

  52 Belmont Ave, Brattleboro, VT 05301
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  /12

  Est $227,000 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  129 West St, Brattleboro, VT 05301

  129 West St, Brattleboro, VT 05301
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  /51

  $949,000

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
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  /33

  $209,000 Sold Jul 11, 2025

  • 1,248 Sq Ft
  • $167/SF
  • 42 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  3 Record Dr, Brattleboro, VT 05301

  This spacious double-wide mobile home offers structural upgrades not often found in park settings. Set on a full poured concrete walk-out basement with I-beam supports and 8" basement walls, the property includes an expansive deck constructed with reinforced framing. Inside, a primary suite with oversized glass stall shower and oversized closet complement an ADA-accessible layout featuring an

  Erica Reynolds Southern Vermont Realty Group

  3 Record Dr, Brattleboro, VT 05301
• 

  

  /40

  Est $343,828 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,716 Sq Ft

  36 Goldfinch Ln, Brattleboro, VT 05301

  36 Goldfinch Ln, Brattleboro, VT 05301
• 

  

  /24

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,183 Sq Ft

  4322 Augur Hole Rd, Brattleboro, VT 05301

  Super location! Easy access to Rt 9 and Rt 30 but tucked into nearly a level acre in a lovely country setting. You can tell the previous occupants loved their gardens and a bit of work would restore the blooms to full glory. The pool is a bonus but is waiting for some care to get up and running...The home has emerged from a fun loving schoolhouse filled with learning and joy to a cozy,

  Christine Lewis Brattleboro Area Realty

  4322 Augur Hole Rd, Brattleboro, VT 05301
• 

  

  /14

  $65,000 Sold Jul 11, 2025

  • 924 Sq Ft
  • $70/SF
  • 70 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  4 Brookwood Dr, West Brattleboro, VT 05301

  Well-maintained single-wide mobile home on a double lot in Tri-Park Coop. Fresh paint and new flooring throughout, newer appliances, and new hot water heater. This home has a light-filled living room, spacious eat-in kitchen, and primary bedroom with half-bath and custom barn door. Enjoy the sounds of the brook from the covered porch and large fenced-in yard with space for gardening. There is a

  Cassandra Ehrlich BHG Masiello Brattleboro

  4 Brookwood Dr, West Brattleboro, VT 05301
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  /32

  Est $333,108 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,363 Sq Ft

  499 S Main St, Brattleboro, VT 05301

  499 S Main St, Brattleboro, VT 05301
• 

  

  /60

  $859,000

  • 4 Beds
  • 3.5 Baths
  • 3,212 Sq Ft

  104 Juniper Ridge Rd, Brattleboro, VT 05301

  Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

  Kristen Ziter Taylor Brattleboro Area Realty

  104 Juniper Ridge Rd, Brattleboro, VT 05301
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  /29

  $269,000 Sold Jul 07, 2025

  • 2,242 Sq Ft
  • $120/SF
  • 65 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  27 Horton Place, Brattleboro, VT 05301

  Outstanding Investment Opportunity Near Downtown Brattleboro. Just minutes from the vibrant Brattleboro town center, this versatile two-unit property offers unmatched convenience and strong potential for investors or owner-occupants alike. Enjoy close proximity to shopping, dining, and professional services, as well as Brattleboro Memorial Hospital, local schools, and several parks for year-round

  Patrice Schneider Southern Vermont Realty Group

  27 Horton Place, Brattleboro, VT 05301
• 

  

  /23

  Est $271,309 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft

  380 S Main St, Brattleboro, VT 05301

  380 S Main St, Brattleboro, VT 05301
• 

  

  /60

  $895,000

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft

  266 Ursa Ridge Rd, Dummerston, VT 05301

  This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

  Randi Ziter Brattleboro Area Realty

  266 Ursa Ridge Rd, Dummerston, VT 05301
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  /33

  $310,000 Sold Jul 03, 2025

  • 1,666 Sq Ft
  • $186/SF
  • 25 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  34 Hampshire Cir, Brattleboro, VT 05301

  Charming home located in peaceful neighborhood setting of Carriage Hill. Move right in to this inviting home located on quiet cul-de-sac. The spacious eat-in kitchen features a breakfast bar and sliding doors leading to a back deck — perfect for morning coffee or summer gatherings. The bright living room boasts a beautiful bay window that fills the space with natural light. The main level

  Carol Slocum Keller Williams Realty Metro-Keene

  34 Hampshire Cir, Brattleboro, VT 05301
• 

  

  /16

  Est $414,423 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,722 Sq Ft

  68 Wilsons Woods Rd, Brattleboro, VT 05301

  68 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /18

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  164 Chestnut St, Brattleboro, VT 05301

  Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
• 

  

  /39

  $312,450 Sold Jul 03, 2025

  • 1,758 Sq Ft
  • $178/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  96 Brattle St, Brattleboro, VT 05301

  Loved and owned by the same family for over 50 years! Very well maintained 1952 Cape with 1 car garage under. This home features first floor bedroom, 2 bedrooms on the second floor. It also has first floor laundry, screen room off the family room, large kitchen and formal living room with fireplace. Two bedrooms and full bath on the second floor round out this wonderful family home. Showings

  Darlene Conca Keller Williams Realty Metro-Keene

  96 Brattle St, Brattleboro, VT 05301
• 

  

  /40

  Est $473,955 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,038 Sq Ft

  67 Wilsons Woods Rd, Brattleboro, VT 05301

  67 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /23

  $1,150,000

  • 6,442 Sq Ft

  69-71 Elliot St, Brattleboro, VT 05301

  Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

  Erica Reynolds Southern Vermont Realty Group

  69-71 Elliot St, Brattleboro, VT 05301
• 

  

  /18

  $420,000 Sold Jun 30, 2025

  • 2,880 Sq Ft
  • $146/SF
  • 88 Days On Market

  • 6 Beds
  • Built 1970

  238 Marlboro Rd, Brattleboro, VT 05301

  This 6-unit fully-leased and cashflowing property is in great condition. With gross rents of $66,000, expenses (including property taxes) of $14,538, and net income of $51,462, this investment property shows a 12.1% cap rate. With stable, long-term tenants on annual leases and fully-separated utilities in 5 of the 6 units, just about everything is taken care of. Built in 1970, the property is

  Steve Schoppmeyer BHG Masiello Brattleboro

  238 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /30

  Est $377,701 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  49 Marlboro Ave, Brattleboro, VT 05301

  49 Marlboro Ave, Brattleboro, VT 05301
• 

  

  /16

  $488,875

  • 5 Beds
  • 4 Baths
  • 3,064 Sq Ft

  176 High St, Brattleboro, VT 05301

  Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

  Susan Bellville Bellville Realty

  176 High St, Brattleboro, VT 05301
• 

  

  /35

  $322,280 Sold Jun 27, 2025

  • 1,544 Sq Ft
  • $209/SF
  • 7 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1871

  108 Chestnut St, Brattleboro, VT 05301

  Charming Traditional New England cape built in 1871 with many upgrades. Located on a lovely cul-de-sac street. Enter through your classic mudroom, with a newly replaced floor, into a fabulous renovated kitchen that has a retro flare with lively yellow tile, & framed black & white tile backsplash. The kitchen is impressive with a nook & granite table & a combination of closed cabinets & open oak

  Kristen Ziter Taylor Brattleboro Area Realty

  108 Chestnut St, Brattleboro, VT 05301
• 

  

  /24

  Est $495,573 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  89 Oak Grove Ave, Brattleboro, VT 05301

  89 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /26

  $725,000

  • 18 Beds
  • 8 Baths
  • 4,932 Sq Ft

  29 Canal St, Brattleboro, VT 05301

  High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1brA new owner can step into to

  Michael Gilman 3GEN Real Estate Inc

  29 Canal St, Brattleboro, VT 05301

Showing Results 41 - 80, Page 2 of 18